EP1335722B1 - Derivés indole-sulfoniques pour le traitement de troubles du snc - Google Patents

Derivés indole-sulfoniques pour le traitement de troubles du snc Download PDF

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Publication number
EP1335722B1
EP1335722B1 EP01997304A EP01997304A EP1335722B1 EP 1335722 B1 EP1335722 B1 EP 1335722B1 EP 01997304 A EP01997304 A EP 01997304A EP 01997304 A EP01997304 A EP 01997304A EP 1335722 B1 EP1335722 B1 EP 1335722B1
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European Patent Office
Prior art keywords
indole
chloro
piperazin
chlorobenzenesulfonyl
formula
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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EP01997304A
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German (de)
English (en)
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EP1335722A2 (fr
Inventor
Steven Mark GlaxoSmmithKline BROMIDGE
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SmithKline Beecham Ltd
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SmithKline Beecham Ltd
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Priority claimed from GB0028708A external-priority patent/GB0028708D0/en
Priority claimed from GB0113517A external-priority patent/GB0113517D0/en
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Publication of EP1335722A2 publication Critical patent/EP1335722A2/fr
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/22—Anxiolytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia

Claims (10)

  1. Composé de formule (I) ou un de ses sels pharmaceutiquement acceptables :
    Figure imgb0043
     formule dans laquelle :
    P représente un groupe phényle, naphtyle ou hétéroaryle ;
    R1 représente un atome de chlore ou de brome ou un groupe cyano ;
    R2 représente un atome d'halogène, un groupe alkyle en C1 à C6, cycloalkyle en C3 à C6, alkoxy en C1 à C6, alkylthio en C1 à C6, alkylsulfinyle en C1 à C6, alkylsulfonyle en C1 à C6, alcanoyle en C1 à C6, CN, CF3, OCH2CF3, OCF3, hydroxy, hydroxyalkyle en C1 à C6, hydroxyalkoxy en C1 à C6, (alkoxy en C1 à C6) carbonyle, (alkoxy en C1 à C6) (alkoxy en C1 à C6), nitro, amino, N (alkyle en C1 à C6)2, NH (alkyle en C1 à C6), alkylamino en C1 à C6 ou di (alkyle en C1 à C6) amino ; ou bien
    R2 représente un groupe C(O)OR4, CONR5R6 ou NR5COR6, dans lequel R4 représente l'hydrogène ou un groupe alkyle en C1 à C6, et R5 et R6 représentent indépendamment l'hydrogène, un groupe alkyle en C1 à C6 ou bien R5 et R6 sont combinés l'un à l'autre pour former un noyau azacyclique penta- à heptagonal contenant facultativement un hétéroatome supplémentaire choisi entre l'azote, le soufre et l'oxygène ; ou bien
    R2 représente un groupe phényle, naphtyle ou hétéroaryle facultativement substitué avec un substituant halogéno, alkyle en C1 à C6, alkoxy en C1 à C6, alcanoyle en C1 à C6, CN, CF3, OCF3, phényloxy, benzyloxy ou cycloalkyloxy en C3 à C6 ;
    R3 représente un noyau hétérocyclique penta- à heptagonal ou un noyau hétérocyclique bicyclique contenant 1 à 3 hétéroatomes choisis entre l'azote, le soufre et l'oxygène, lesdits noyaux étant facultativement substitués avec un ou plusieurs groupes alkyle en C1 à C6;
    m est égal à 1 ou 2 ; ou
    n a une valeur de 0 à 5.
  2. Composé suivant la revendication 1, dans lequel R3 représente un noyau pipérazine non substitué.
  3. Composé suivant la revendication 1 ou 2, dans lequel m est égal à 1 et R1 représente un groupe chloro en position 5 du noyau indole.
  4. Composé suivant l'une quelconque des revendications 1 à 3, dans lequel m est égal à 2 et R1 représente un groupe 5,7-dichloro.
  5. Composé suivant l'une quelconque des revendications 1 à 4, dans lequel P représente un groupe phényle.
  6. Composé suivant l'une quelconque des revendications 1 à 5, dans lequel n est égal à 1 et R2 représente le chlore.
  7. Composé suivant la revendication 1, qui est le 5-chloro-1-(3-chloro-benzènesulfonyl)-4-pipérazine-1-yl-1H-indole ;
    5-chloro-1-(3,5-dichlorobenzènesulfonyl)-4-pipérazine-1-yl-1H-indole ;
    5-chloro-1-(2,6-dichlorobenzènesulfonyl)-4-pipérazine-1-yl-1H-indole ;
    5-chloro-1-(naphtalène-2-sulfonyl)-4-pipérazine-1-yl-1H-indole ;
    5-chloro-1-(3,5-dichloro-2-méthoxybenzènesulfonyl)-4-pipérazine-1-yl-1H-indole ;
    5-chloro-1-(3-chlorobenzènesulfonyl)-4-pipérazine-1-yl-1H-indole ;
    1-(benzènesulfonyl)-5-chloro-4-pipérazine-1-yl-1H-indole ;
    5-chloro-1-(2,6-difluorobenzènesulfonyl)-4-pipérazine-1-yl-1H-indole ;
    1-(2-bromobenzènesulfonyl)-5-chloro-4-pipérazine-1-yl-1H-indole ;
    5-chloro-1-(2-chlorobenzènesulfonyl)-4-pipérazine-1-yl-1H-indole ;
    5-chloro-1-(3-trifluorométhyl-benzènesulfonyl)-.4-pipérazine-1-yl-lh-indole ;
    5-chloro-1-(3-méthylbenzènesulfonyl)-4-pipérazine-1-yl-1H-indole ;
    1-(3-bromobenzènesulfonyl)-5-chloro-4-pipérazine-1-yl-1H-indole ;
    1-(4-bromo-2-trifluorométhoxybenzènesulfonyl)-5-chloro-4-pipérazine-1-yl-1H-indole ;
    5-chloro-1-(3-cyanobenzènesulfonyl)-4-pipérazine-1-yl-1H-indole ;
    5-chloro-1-(1-naphtalènesulfonyl)-4-pipérazine-1-yl-1H-indole ;
    5-chloro-1-(2,5-difluorobenzènesulfonyl)-4-pipérazine-1-yl-1H-indole ;
    5-chloro-1-(4-fluorobenzènesulfonyl)-4-pipérazine-1-yl-1H-indole ;
    5-chloro-1-(4-chlorobenzènesulfonyl)-4-pipérazine-1-yl-1H-indole ;
    5-chloro-1-(1,3,5-triméthyl-1H-pyrazole-4-sulfonyl)-4-pipérazine-1-yl-1H-indole ;
    5-chloro-1-(pyridine-2-sulfonyl)-4-pipérazine-1-yl-1H-indole ;
    5-chloro-1-(2,5-diméthylbenzènesulfonyl)-4-pipérazine-1-yl-1H-indole ;
    3-chloro-1-(3-chlorobenzènesulfonyl)-4-pipérazine-1-yl-1H-indole ;
    7-chloro-1-(3-chlorobenzènesulfonyl)-4-pipérazine-1-yl-1H-indole ;
    7-chloro-1-(3,5-dichlorobenzènesulfonyl).-4-pipérazine-1-yl-1H-indole ;
    1-benzènesulfonyl-7-chloro-4-pipérazine-1-yl-1H-indole ;
    1-(4-bromo-2-trifluorométhoxybenzènesulfonyl)-7-chloro-4-pipérazine-1-yl-1H-indole ;
    7-bromo-1-(3-chlorobenzènesulfonyl)-4-pipérazine-1-yl-1H-indole ;
    7-cyano-1-(3-chlorobenzènesulfonyl)-4-pipérazine-1-yl-1H-indole ;
    1-(3-chlorobenzènesulfonyl)-3,5-dichloro-4-pipérazine-1-yl-1H-indole ;
    1-(3-chlorobenzènesulfonyl)-5,7-dichloro-4-pipérazine-1-yl-1H-indole ;
    5-chloro-1-(3-chlorobenzènesulfonyl)-4-[1,4]diazépan-1-yl-1H-indole ;
    5-chloro-1-(3-chlorobenzènesulfonyl)-4-((R)-3-méthylpipérazine-1-yl)-1H-indole ;
    5-chloro-1-(3-chlorobenzènesulfonyl)-4-((S)-3-méthylpipérazine-1-yl)-1H-indole ;
    1-(3-chlorobenzènesulfonyl)-5-cyano-4-pipérazine-1-yl-1H-indole ;
    6-chloro-1-(3-chlorobenzènesulfonyl)-4-pipérazine-1-yl-1H-indole ;
    5-chloro-1-(4-chloro-2-trifluorométhoxybenzènesulfonyl)-4-pipérazine-1-yl-1H-indole ;
    1-(4-bromo-2-cyanobenzènesulfonyl)-5-chloro-4-pipérazine-1-yl-1H-indole ;
    7-chloro-1-(3-chlorobenzènesulfonyl)-4-[1,4]diazépan-1-yl-1H-indole ;
    ou un de ses sels pharmaceutiquement acceptables.
  8. Composition pharmaceutique comprenant un composé de formule (I) répondant à la définition figurant dans l'une quelconque des revendications 1 à 7 ou un de ses sels pharmaceutiquement acceptables et un support ou excipient pharmaceutiquement acceptable.
  9. Utilisation d'un composé de formule (I) répondant à la définition figurant dans l'une quelconque des revendications 1 à 7 dans la production d'un médicament destiné au traitement de la dépression, de l'anxiété, de troubles cognitifs de la mémoire, de la maladie d'Alzheimer, du déclin cognitif dû à l'âge, de l'altération cognitive faible, du syndrome de déficit d'attention/ hyperactivité et/ou de la schizophrénie.
  10. Procédé pour la préparation d'un composé de formule (I) répondant à la définition figurant dans la revendication 1 ou d'un de ses sels pharmaceutiquement acceptables, procédé qui comprend
    (a) le couplage d'un composé de formule (II) :
    Figure imgb0044
     dans laquelle R1, R3 et m répondent aux définitions mentionnées pour la formule (I) ou de ses dérivés protégés avec un composé de formule (III)
    Figure imgb0045
     dans laquelle P, R2 et n répondent aux définitions mentionnées pour la formule (I) ou un de ses dérivés protégés et L représente un groupe partant, et ensuite facultativement :
    • l'élimination de tous les groupes protecteurs,
    • la formation d'un sel pharmaceutiquement acceptable ;
    (b) la préparation d'un composé de formule (I) dans laquelle R3 représente un groupe pipérazinyle ou 1,4-diazépanyle facultativement substitué lié au groupement indole par un atome d'azote, qui comprend la réaction d'un composé de formule (IV)
    Figure imgb0046
     dans laquelle R1, R2 , P, m et n répondent aux définitions mentionnées pour la formule (I), ou d'un de ses dérivés protégés, et L2 représente un groupe partant convenable (par exemple un atome d'halogène, tel qu'un atome de brome, ou un groupe trifluorométhylsulfonyloxy ou nonafluorobutylsulfonyloxy), avec un composé de formule R3' -H, dans laquelle R3' représente un groupe pipérazinyle ou 1,4-diazépanyle facultativement protégé et/ou substitué, et ensuite, facultativement .
    • l'élimination de tous les groupes protecteurs,
    • la formation de sels pharmaceutiquement acceptables, ou
    (c) la suppression de la protection d'un composé de formule (I) qui est protégé ; ou
    (d) l' interconversion d'un composé de formule (I) en d'autres composés de formule (I).
EP01997304A 2000-11-24 2001-11-16 Derivés indole-sulfoniques pour le traitement de troubles du snc Expired - Lifetime EP1335722B1 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
GB0028708 2000-11-24
GB0028708A GB0028708D0 (en) 2000-11-24 2000-11-24 Novel compounds
GB0113517A GB0113517D0 (en) 2001-06-04 2001-06-04 Novel Compounds
GB0113517 2001-06-04
PCT/EP2001/013411 WO2002041889A2 (fr) 2000-11-24 2001-11-16 Composes utiles pour le traitement de troubles du snc

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EP1335722A2 EP1335722A2 (fr) 2003-08-20
EP1335722B1 true EP1335722B1 (fr) 2006-08-30

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US (1) US20050176705A1 (fr)
EP (1) EP1335722B1 (fr)
JP (1) JP2004517072A (fr)
AT (1) ATE337780T1 (fr)
AU (1) AU2002220715A1 (fr)
DE (1) DE60122767T2 (fr)
ES (1) ES2271124T3 (fr)
WO (1) WO2002041889A2 (fr)

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US6818639B2 (en) * 2000-07-21 2004-11-16 Biovitrum Ab Pharmaceutical combination formulation and method of treatment with the combination
EP1326830A1 (fr) * 2000-10-20 2003-07-16 Biovitrum Ab N1-(benzensulfonyl)indoles substitues en 2, 3, 4 ou 5 et leur utilisation a des fins de traitement

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DE60122767T2 (de) 2007-09-13
WO2002041889A2 (fr) 2002-05-30
AU2002220715A1 (en) 2002-06-03
WO2002041889A3 (fr) 2003-04-10
ES2271124T3 (es) 2007-04-16
EP1335722A2 (fr) 2003-08-20
ATE337780T1 (de) 2006-09-15
US20050176705A1 (en) 2005-08-11
JP2004517072A (ja) 2004-06-10
DE60122767D1 (de) 2006-10-12

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